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Compare 140 Vacation Homes in Kailua with updated reviews, rates, and availability.

Fisher's Hana Bay Hale, Across from Hana Bay

9.4 out of 10, Exceptional, (363)
"Great location and the place had everything we needed for our family. Could use some updates and fixes, but a good price for Hana. We appreciated the beach gear and the kids didn't want to leave."
The price is AED 716
AED 1,442 total
includes taxes & fees
30 Mar - 31 Mar
Fisher's Hana Bay Hale, Across from Hana Bay

STHA-2017/0002 Across from Hana Bay

9.6 out of 10, Exceptional, (363)
"great place, quiet, nice location. perfect."
The price is AED 639
AED 1,308 total
includes taxes & fees
6 Apr - 7 Apr
STHA-2017/0002 Across from Hana Bay

Kaiholo Hale

3.0 star property
9.4 out of 10, Exceptional, (195)
"A perfect area and a perfect stay! The hosts think of everything and even include some nice touches like banana bread and chocolates. The property is immaculate and the condo is extremely comfortable. We would recommend this property to anyone."
Kaiholo Hale

Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many amenities

10.0 out of 10, Exceptional, (215)
"I have stayed in many rental homes and this is by far the best equipped rental home I have ever stayed in. We love to cook and usually can’t find enough pots and pans and utensils and this house had them all.We also had the privilege of their neighbors having goats and baby goats and cows which we enjoyed seeing from the deck of the house The house was also close enough to major towns And easy to find I would definitely stay here again on our next trip to Maui "
Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many amenities

Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!

9.8 out of 10, Exceptional, (219)
"This was our 3rd time staying out in Hana for 2 nights on the front end of our family vacation to Maui. The location of this house is great as it is just a short distance off the highway and the property is beautiful. Had everything we needed for our brief stay and was comfortable. "
The price is AED 1,286
AED 2,563 total
includes taxes & fees
6 Apr - 7 Apr
Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!

Maui Sunset Resort A102 - Aloha Mai, Remodel, Ground floor, 1BR/2BA, Sleeps 5, A

9.6 out of 10, Exceptional, (96)
"Enjoyed our stay, the pool and hot tub as well. Centrally located, so it was easy to find our way around."
Maui Sunset Resort A102 - Aloha Mai, Remodel, Ground floor, 1BR/2BA, Sleeps 5, A

Beautiful Home in paradise!

9.6 out of 10, Exceptional, (162)
"We so enjoyed our stay here. Both King beds were very comfortable, the garden is gorgeous and the house was large and comfortable. "
The price is AED 1,451
AED 2,631 total
includes taxes & fees
30 Mar - 31 Mar
Beautiful Home in paradise!

Gorgeous Home Across from Beach - 5 BR + Opt. Cottage / 4 Bath / AC

10.0 out of 10, Exceptional, (116)
"Close to Beaches, Shopping, Awesome Restaurants, we had a blast!"
Gorgeous Home Across from Beach - 5 BR + Opt. Cottage / 4 Bath / AC

Mountain to Ocean Views Pole House @ Maui Adventure Villa

9.8 out of 10, Exceptional, (214)
"Incredible week at this beautiful home. John was very accommodating and went above and beyond to make sure we enjoyed our stay and had everything we needed. Couldn’t have been more pleased with our experience."
Mountain to Ocean Views Pole House @ Maui Adventure Villa

Waterfall House - Private House Overlooking the Ocean!

9.8 out of 10, Exceptional, (24)
"Pros: Incredible setting and the grounds are beautiful. Whale watching from the hot tub was probably the highlight of our trip. The pool gets the perfect amount of sun on the nice days. The whole property is very calm and relaxing. The people onsite are incredibly friendly and do not disturb the guests.Cons:The circle bed in the listing photos in incredibly uncomfortable. Getting in and out you or rolling or kneeling on marble to get on a mattress that has seen better decades. We would've slept...
Waterfall House - Private House Overlooking the Ocean!

Tropical Gated Oceanfront Estate, Pool, Privacy, and huge ocean view on 2/3 acre

9.8 out of 10, Exceptional, (194)
"great for large groups"
Tropical Gated Oceanfront Estate, Pool, Privacy, and huge ocean view on 2/3 acre

Luxury Upcountry Villa with breathtaking views

10.0 out of 10, Exceptional, (37)
"This place is great. The views are incredible. We had a great time here and would have loved to stay longer. Watching the sunset from the hot tub, cooling down in the pool afterwards, lying in bed watching the moon set in the mornings. The quiet and peacefulness of the upcountry. Memories we will never forget."
Luxury Upcountry Villa with breathtaking views

OCEANFRONT HOME*UNINTERRUPTED*HOT TUB*PRIVATE GEM

9.8 out of 10, Exceptional, (7)
"We could not be more grateful for our experience in this home. Steps from our lawn was a beautiful beach with unforgettable sunsets on the beach or the fully open air lanai. The home was perfectly and newly appointed, spotless, and comfortable. The management team facilitated an easy check in and also checked in while we were there. Thank you! We’ll be bac!"
OCEANFRONT HOME*UNINTERRUPTED*HOT TUB*PRIVATE GEM

North Shore Ocean View Cottage

10.0 out of 10, Exceptional, (136)
"We love this property! Our standards are high when it comes to cleanliness and updated finishes/fixtures and linens. It’s quiet and private. Brigitte and Dave are great and were extremely welcoming and helpful with questions or recommendations for our Maui stay. Many properties just don’t match what this cottage has to offer. Quality is top notch in our view. Second visit and we would stay again in a heartbeat. Thanks Dave and Brigitte!!"
North Shore Ocean View Cottage

Kula Luxury Retreat With Stunning Ocean & Mountain Views!

10.0 out of 10, Exceptional, (70)
"KeoKea ranch is beautiful. The hosts are super responsive and very nice. If you like quiet and incredible views and some four leggeds to entertain you, just do it!"
Kula Luxury Retreat With Stunning Ocean & Mountain Views!

Sugar Beach Resort condo with ocean view, AC - surf, bike & golf

8.8 out of 10, Excellent, (48)
"All good, except the screen doors need to be fixed."
Sugar Beach Resort condo with ocean view, AC - surf, bike & golf

Tropical Garden Family Home - Sleeps 6 - Walk to Beach, BBQ, Hot Tub

9.6 out of 10, Exceptional, (106)
"Nice property with plenty of space, great location on the island, super communicative and polite host, and such a great backyard/outdoor area. Would highly recommend!"
The price is AED 1,414
AED 4,269 total
includes taxes & fees
8 Apr - 9 Apr
Tropical Garden Family Home - Sleeps 6 - Walk to Beach, BBQ, Hot Tub

Historic Upcountry Maui Property With Pool, 5 Bedrooms, Sleeps 16

10.0 out of 10, Exceptional, (61)
"16 of us stayed at this beautiful property. Two Families, 12 children total. We have nothing bad to say. All of our expectations were met. The listing is true and accurate. Communication with the property manager was always prompt and efficient.We would definitely stay her again."
The price is AED 5,124
AED 10,079 total
includes taxes & fees
19 Apr - 20 Apr
Historic Upcountry Maui Property With Pool, 5 Bedrooms, Sleeps 16

BEACHFRONT MAUI KIHEI HOUSE

9.8 out of 10, Exceptional, (157)
"The property is beautiful. We had a family gathering of kids and grandkids. The space fit our family’s needs well. There is a large grass area between the house and beach. You can play volleyball, bags, and croquet. The beach was a minute walk from the house. The Maui sunsets were spectacular. Not a good swimming beach but a wonderful beach for exploring and watching the sea turtles come out and rest on the rocky sand. "
BEACHFRONT MAUI KIHEI HOUSE

Stunning Beach Front Townhouse

10.0 out of 10, Exceptional, (89)
"We had the please of spending 6 nights at this amazing unit. Location is perfect for getting around the island. Amenities were exceptional everything we needed and then some was available. Beds were extremely comfortable and the kids loved the space upstairs to themselves. Pool, parking, beach access and local attractions made this place even more amazing. Would highly recommend!!!"
Stunning Beach Front Townhouse
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Kailua

Sugar Beach Resort

3.0 star property
8.6 out of 10, Excellent, (1047)
"The view was beautiful from the balcony as it was right on the beach. Unit was very clean and had everything you needed for an enjoyable vacation. The king bed was comfortable and it is always nice to have a washer & dryer. The one recommendation I would make would be to upgrade the living room furniture as it is very uncomfortable and outdated. "
Sugar Beach Resort

Maui Beach Vacation Club

2.5 star property
8.4 out of 10, Very Good, (734)
"Great for family"
Maui Beach Vacation Club

Maui Sunset

3.5 star property
8.8 out of 10, Excellent, (419)
"The outside areas were well maintained. Nice pool/hot tub area. "
Maui Sunset
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.